Mirror-Image Asymmetry (eBook)

JAMES P. RIEHL received a BS degree in chemistry from Villanova University in 1970 and a PhD in physical chemistry from Purdue University in 1975. He is currently Dean of the Swenson College of Science and Engineering and Professor of Chemistry at the University of Minnesota Duluth, a position he has held since 2000. Dr. Riehl is a frequent invited speaker nationally and internationally on the topic of molecular chirality, and is the author of numerous research publications in the applications of optical spectroscopy to the study of chiral structures. He was the recipient of the St. Louis Award of the American Chemical Society for his outstanding contributions to the chemistry profession, and currently holds a University of Minnesota McKnight Presidential Leadership Chair.

Preface xi

List of Figures and Biographic Photographs xv

1 The Mirror Image 1

Handedness 2

The Symmetry of Nonsuperimposable Mirror Images 5

Nomenclature for Chiral Molecules 11

Nomenclature for Dissymmetric and Other Chiral Molecules 19

Summary 24

Suggestions for Further Reading 24

References 25

List of Biographic Photographs, Sidebars, and Figures 25

2 Molecular Chirality in Living Systems 27

Optical Rotation 30

From Biot to Pasteur 36

Biochemical Homochirality 44

Determination of Absolute Structures of Chiral Molecules 52

Summary 54

Suggestions for Further Reading 55

References 55

List of Biographic Photographs, Sidebars, and Figures 56

3 The Origin of Chirality in Living Systems 59

Must Life be Chiral? 60

Mirror-image life? 62

The Origin of Homochirality in Living Systems 63

Extraterrestrial Chirality 65

Nuclear Chirality 70

Other Extraterrestrial Sources 72

The Beginning of Life on Earth: Biochemistry 73

Getting Started in the Right (or Left) Direction 76

Summary 78

Suggestions for Further Reading 78

References 79

List of Sidebars and Figures 80

4 Chiral Chemistry, Recognition, and Control in Living Systems 81

Chiral Chemical Evolution 81

Chiral Recognition at the Molecular Level 83

Examples of Chiral Recognition and Discrimination 87

Smell 87

Taste 91

Communication 93

Chirality as a Control Mechanism in Biochemistry 104

Summary 108

Suggestions for Further Reading 108

References 108

List of Biographic Photographs, Sidebars, and Figures 110

5 Chirality and Drugs 111

Chirality in Natural Remedies and Folk Medicines 112

Enantiomeric Differences in Natural Products 114

Thalidomide and Regulation of Chiral Drugs 118

Chirality and Drug Activity 121

Ibuprofen 121

Prozac 122

Cialis 123

Nexium 125

Lipitor 128

Chiral Switching 129

Ephedrine, Pseudoephedrine, and Methamphetamine 131

Preparation of Pure Enantiomers 135

Summary 143

Suggestions for Further Reading 143

References 143

List of Biographic Photographs, Sidebars, and Figures 145

6 The Chirality of Living Systems 147

Preliminary Cautions 148

Chirality in Nature 153

Classification of Plant and Animal Chirality (Asymmetry) 159

Symmetric Life 160

Racemic Life 160

Asymmetric Life 162

Homo sapiens Asymmetry 170

Summary 171

Suggestions for Further Reading 171

References 172

List of Sidebars and Figures 173

7 The Handedness of Homo sapiens 175

Are You Right-Handed or Left-Handed? 176

The Statistics of Handedness 178

The Origin of Left-Handedness 183

The Human Genetics of Handedness 186

Summary 192

Suggestions for Further Reading 193

References 194

List of Sidebars and Figures 195

8 Living in a Right-Hander's World 197

Clockwise and Counterclockwise (or Anticlockwise) Rotation 198

Helical Stairways 201

Around the House 204

Making Music Left-Handed 205

The Chirality of Writing 207

Sports and the Left-Hander 210

American Baseball: The Chiral Sport 216

Driving on the Left or Right Side 221

Windmills 224

Summary 227

Suggestions for Further Reading 228

References 228

List of Sidebars and Figures 228

9 The Asymmetric Universe 231

List of Figures 234

Appendix 235

Biography 239

Index 241

"Riehl should be commended for presenting an understable introduction to chirality to such a wide audience." (Choice, October 2010).